Carbanilides used as pesticides

ABSTRACT

The invention concerns novel carbanilides of formula (I),in which A, Q, R, X, Z and m have the meanings given in the description. The invention further concerns a plurality of processes for preparing these substances, and their use as microbicides for controlling undesirable microorganisms both in crop protection and in the protection of materials. Additionally, they are suitable for controlling animal pests.

This application is a 371A PCT/EP97/03694 filed Jul. 11, 1997.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to novel carbanilides, to a plurality ofprocesses for their preparation and to their use for controlling plantand animal pests.

BACKGROUND OF THE INVENTION

It is already known that numerous carboxamides have fungicidalproperties (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0589 313). The activity of these compounds is good, but in some casesleaves something to be desired.

DETAILED DESCRIPTION OF THE INVENTION

This invention, accordingly, provides novel carbanilides of the formula

in which

R represents halogen, nitro, cyano, alkyl having 1 to 8 carbon atoms,halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms,alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbonatoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms,halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms,alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbonatoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkylmoiety,

m represents numbers 0, 1, 2, 3 or 4,

A represents a radical of the formula

R¹ represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms and

R² represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbonatoms, or

A represents a radical of the formula

R³ and R⁴ independently of one another each represent hydrogen, halogen,alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms and

R⁵ represents halogen, cyano, alkyl having 1 to 4 carbon atoms orhalogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or

A represents a radical of the formula

R⁶ and R⁷ independently of one another each represent hydrogen, halogen,alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms and

R⁸ represents hydrogen, alkyl having 1 to 4 carbon atoms or representshalogen, or

A represents a radical of the formula

R⁹ represents halogen, cyano, alkyl having 1 to 6 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms orrepresents halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5halogen atoms, or

A represents a radical of the formula

R¹⁰ represents halogen, cyano, alkyl having 1 to 4 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atomsor represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5halogen atoms and

R¹¹ represents hydrogen, halogen, cyano, alkyl having 1 to 4 carbonatoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogenatoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbonatoms or represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5halogen atoms, or

A represents a radical of the formula

R¹² represents alkyl having 1 to 4 carbon atoms or representshalogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,

X¹ represents a sulphur atom, represents SO, SO₂ or —CH₂, or

A represents a radical of the formula

R¹³ represents alkyl having 1 to 4 carbon atoms or representshalogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or

A represents a radical of the formula

R¹⁴ represents halogen, cyano, alkyl having 1 to 4 carbon atoms orhalogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or

A represents a radical of the formula

R¹⁵ and R¹⁶ independently of one another each represent hydrogen,halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4carbon atoms and 1 to 5 halogen atoms and

R¹⁷ represents hydrogen, halogen or alkyl having 1 to 4 carbon atoms, or

A represents a radical of the formula

R¹⁸ represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4carbon atoms and

R¹⁹ represents halogen, alkyl having 1 to 4 carbon atoms orhalogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or

A represents a radical of the formula

R²⁰ represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4carbon atoms and

R²¹ represents halogen, alkyl having 1 to 4 carbon atoms orhalogenoalkyl having 1 to 4 carbons and 1 to 5 halogen atoms, or

A represents a radical of the formula

R²² represents hydrogen or alkyl having 1 to 4 carbon atoms and

R²³ represents halogen or alkyl having 1 to 4 carbon atoms, or

A represents a radical of the formula

Q represents alkylene having 1 to 4 carbon atoms, alkenylene having 2 to4 carbon atoms, alkinylene having 2 to 4 carbon atoms or a group of theformula

 in which

R²⁴, R²⁵ and R²⁶ independently of one another each represent hydrogen,alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms,alkenyl having 2 to 4 carbon atoms or alkinyl having 2 to 4 carbonatoms, or

Q represents a group of the formula

R²⁷ and R²⁸ independently of one another each represent hydrogen oralkyl having 1 to 4 carbon atoms,

Y represents an oxygen atom or represents S(O)_(r), where

r represents the numbers 0, 1 or 2, and

n and p independently of one another each represent the numbers 0, 1 or2,

where the molecular moiety labelled (*) is in each case attached to thephenyl radical of the aniline moiety,

X represents oxygen or sulphur and

Z represents optionally substituted phenyl, optionally substitutednaphthyl, optionally substituted anthracenyl or represents optionallysubstituted hetaryl.

Furthermore, it has been found that carbanilides of the formula (I) areobtained when

a) acyl halides of the formula

 in which

A and X are each as defined above and

Hal represents halogen

are reacted with aniline derivatives of the formula

 in which

Q, R, Z and m are each as defined above,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent, or

b) carbanilide derivatives of the formula

 in which

A, R, X and m are each as defined above and

X² represents oxygen or sulphur,

are reacted with compounds of the formula

 in which

R²⁸, Z and p are each as defined above and

E represents a leaving group,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent, or

c) carbanilide derivatives of the formula

 in which

A, R, R²⁷, X and m are each as defined above and

E¹ represents a leaving group

are reacted with compounds of the formula

 in which

R²⁸, Z and p are each as defined above and

X³ represents oxygen or sulphur,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent, or

d) carbanilide derivatives of the formula

 in which

A, R, R²⁷, X and m are each as defined above

are reacted with compounds of the formula

 in which

R²⁸, Z and p are each as defined above and

E represents a leaving group,

if appropriate in the presence of an acid binder and if appropriate inthe presence of a diluent or,

e) carbanilide derivatives of the formula

 in which

A, R, R²⁶, X and m are each as defined above

are reacted with hydroxylamine derivatives of the formula

H₂N—O—Z  (X)

 in which

Z is as defined above,

if appropriate in the presence of a catalyst and if appropriate in thepresence of a diluent.

Finally, it has been found that the novel carbanilides of the formula(I) are very suitable for use as pesticides. They have microbicidalproperties and can be employed for controlling undesirablemicroorganisms both in crop protection and in the protection ofmaterials. Additionally, they are suitable for controlling animal pests.

Surprisingly, the carbanilides of the formula (I) according to theinvention have considerably better fungicidal activity than theconstitutionally most similar prior-art carboxamides of the samedirection of action.

The formula (I) provides a general definition of the carbanilidesaccording to the invention.

R preferably represents fluorine, chlorine, bromine, nitro, cyano, alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbonatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms,alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbonatoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety orrepresents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxymoiety and 1 to 4 carbon atoms in the alkyl moiety.

m preferably represents the numbers 0, 1, 2 or 3, where R representsidentical or different radicals if m represents 2 or 3.

A preferably represents a radical of the formula

R¹ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,isopropyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms and

R² represents hydrogen, fluorine, chlorine, bromine, iodine, methyl orethyl.

A furthermore preferably represents a radical of the formula

R³ and R⁴ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and

R⁵ represents fluorine, chlorine, bromine, cyano, methyl, ethyl orhalogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms.

A furthermore preferably represents a radical of the formula

R⁶ and R⁷ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and

R⁸ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

A furthermore preferably represents a radical of the formula

R⁹ represents fluorine, chlorine, bromine, iodine, cyano, alkyl having 1to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms orrepresents halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms.

A furthermore preferably represents a radical of the formula

R¹⁰ represents fluorine, chlorine, bromine, iodine, cyano, methyl,ethyl, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio orrepresents halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms and

R¹¹ represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,methyl, ethyl, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio,ethylthio or represents halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 fluorine, chlorine and/or bromine atoms.

A furthermore preferably represents a radical of formula

R¹² represents methyl, ethyl or halogenoalkyl having 1 or 2 carbon atomsand 1 to 5 fluorine, chlorine and/or bromine atoms and

X¹ represents a sulphur atom, represents SO, SO₂ or —CH₂—.

A furthermore preferably represents a radical of formula

R¹³ represents methyl, ethyl or halogenoalkyl, having 1 or 2 carbonatoms and 1 to 5 fluorine, chlorine and/or bromine atoms.

A furthermore preferably represents a radical of the formula

R¹⁴ represents fluorine, chlorine, bromine, cyano, methyl, ethyl orhalogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms.

A furthermore preferably represents a radical of the formula

R¹⁵ and R¹⁶ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and

R¹⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

A furthermore preferably represents a radical of the formula

R¹⁸ represents hydrogen, fluorine, chlorine, bromine, amino, cyano,methyl or ethyl and

R¹⁹ represents fluorine, chlorine, bromine, methyl, ethyl orhalogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms.

A furthermore preferably represents a radical of the formula

R²⁰ represents hydrogen, fluorine, chlorine, bromine, amino, cyano,methyl or ethyl and

R²¹ represents fluorine, chlorine, bromine, methyl, ethyl orhalogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms.

A furthermore preferably represents a radical of the formula

R²² represents hydrogen, methyl or ethyl and

R²³ represents fluorine, chlorine, bromine, methyl or ethyl.

A furthermore preferably represents a radical of the formula

Q preferably represents alkylene having 1 to 3 carbon atoms, alkenylenehaving 2 or 3 carbon atoms, alkinylene having 2 or 3 carbon atoms orrepresents a group of the formula

R²⁴, R²⁵ and R²⁶ independently of one another each represent hydrogen,methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, alkenyl having 2 or3 carbon atoms or alkinyl having 2 or 3 carbon atoms.

Q furthermore preferably represents a group of the formula

R ²⁷ and R²⁸ independently of one another each represent hydrogen,methyl or ethyl,

Y represents an oxygen atom or represents S(O)_(r) where

r represents the numbers 0, 1 or 2 and

n and p independently of one another each represent the numbers 0, 1 or2, where the molecular moiety labelled (*) is in each case attached tothe phenyl radical of the aniline moiety.

X also preferably represents oxygen or sulphur.

Z preferably represents phenyl, naphthyl or anthracenyl, where each ofthese radicals may be mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen, alkyl having1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 5 fluorine, chlorine and/or bromine atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, phenyl and phenoxy.

Z furthermore preferably represents hetaryl having 5 or 6 ring membersand 1 to 3 heteroatoms, such as oxygen, sulphur and/or nitrogen, whereeach of the heterocycles may be mono- or disubstituted by identical ordifferent substituents selected from the group consisting of halogen,cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorineand/or bromine atoms, phenyl and phenoxy.

R particularly preferably represents fluorine, chlorine, bromine, nitro,cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl,tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, difluorochloromethylthio, allyloxy, propargyloxy,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl orethoximinoethyl.

m particularly preferably represents the numbers 0, 1 , 2 or 3, where Rrepresents identical or different radicals if m represents 2 or 3.

A particularly preferably represents a radical of the formula

R¹ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,isopropyl, difluoromethyl, trifluoromethyl, difluorochloromethyl ortrichloromethyl and

R² represents hydrogen, fluorine, chlorine, bromine, iodine, methyl orethyl.

A furthermore particularly preferably represents a radical of theformula

R³ and R⁴ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and

R⁵ represents fluorine, chlorine, bromine, cyano, methyl, ethyl,trifluoromethoxy, difluoromethoxy, difluorochloromethoxy ortrichloromethoxy.

A furthermore particularly preferably represents a radical of theformula

R⁶ and R⁷ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and

R⁸ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

A furthermore particularly preferably represents a radical of theformula

R⁹ represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl,n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl,trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,trichloromethoxy, trifluoromethylthio, difluoromethylthio,difluorochloromethylthio or trichloromethylthio.

A furthermore particularly preferably represents a radical of theformula

R¹⁰ represents fluorine, chlorine, bromine, iodine, cyano, methyl,ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl,trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl,methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy,difluoromethoxy, difluorochloromethoxy or trichloromethoxy and

R¹¹ represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl,tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl,trichloromethyl, methoxy, ethoxy, methylthio, ethylthio,trifluoromethoxy, difluoromethoxy, difluorochloromethoxy ortrichloromethoxy.

A furthermore particularly preferably represents a radical of theformula

R¹² represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl and

X¹ represents a sulphur atom, represents SO, SO₂ or —CH₂—.

A furthermore particularly preferably represents a radical of theformula

R¹³ represents methyl, ethyl, trifluoromethyl, difluoromethyl,difluorochloromethyl or trichloromethyl.

A furthermore particularly preferably represents a radical of theformula

R¹⁴ represents fluorine, chlorine, bromine, cyano, methyl, ethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl.

A furthermore particularly preferably represents a radical of theformula

R¹⁵ and R¹⁶ independently of one another each represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,difluoromethyl, difluorochloromethyl or trichloromethyl and

R¹⁷ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

A furthermore particularly preferably represents a radical of theformula

R¹⁸ represents hydrogen, fluorine, chlorine, bromine, amino, cyano,methyl or ethyl and

R¹⁹ represents fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl.

A furthermore particularly preferably represents a radical of theformula

R²⁰ represents hydrogen, fluorine, chlorine, bromine, amino, cyano,methyl or ethyl and

R²¹ represents fluorine, chlorine, bromine, methyl, ethyltrifluoromethyl, difluoromethyl, difluorochloromethyl ortrichloromethyl.

A furthermore particularly preferably represents a radical of theformula

R²² represents hydrogen, methyl or ethyl and

R²³ represents fluorine, chlorine, bromine, methyl or ethyl.

A furthermore particularly preferably represents a radical of theformula

Q particularly preferably represents alkylene having 1 to 3 carbonatoms, alkenylene having 2 or 3 carbon atoms, alkinylene having 2 or 3carbon atoms or represents a group of the formula

R²⁴, R²⁵ and R²⁶ independently of one another each represent hydrogen,methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl or propargyl.

Q furthermore particularly preferably represents a group of the formula

R²⁷ and R²⁸ independently of one another each represent hydrogen, methylor ethyl,

Y represents an oxygen atom or represents S(O)_(r), where

r represents the numbers 0, 1 or 2, and

n and p independently of one another each represent the numbers 0, 1 or2, where the molecular moiety labelled (*) is in each case attached tothe phenyl radical of the aniline moiety.

X also particularly preferably represents oxygen or sulphur.

Z particularly preferably represents phenyl, naphthyl or anthracenyl,where each of these radicals may be mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, n-butyl, isopropyl, n-butyl,sec-butyl, i-butyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio,trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl,trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,trichloromethoxy, phenyl and phenoxy.

Z furthermore particularly preferably represents pyrrolyl, furyl,pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl,oxadiazolyl, thiadiazolyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, pyridyl, pyrimidyl, pyrazinyl or pyridazinyl, whereeach of these radicals may be mono- or disubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, i-butyl, tert-butyl, methoxy, ethoxy, methylthio,ethylthio, trifluoromethyl, difluoromethyl, difluorochloromethyl,trichloromethyl, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy, trichloromethoxy, phenyl and phenoxy.

Using 3-difluoromethoxy-thiophene-2-carbonyl chloride and2-(2-phenyl-ethen-1-yl)-aniline as starting materials, the course of theprocess (a) according to the invention can be illustrated by theequation below.

Using 2-hydroxy-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide and2,4-dimethylbenzylchloride as starting materials, the course of theprocess (b) according to the invention can be illustrated by theequation below.

Using 2-bromomethyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilideand 4-chloro-thiophenol as starting materials, the course of the process(c) according to the invention can be illustrated by the equation below.

Using2-hydroxymethyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide and2,4-dimethylbenzyl chloride as starting materials, the course of theprocess (d) according to the invention can be illustrated by theequation below.

Using1-methyl-2-methylcarbonyl-3-trifluoromethylpyrazole-4-carboxanilide andO-phenyl-hydroxylamine as starting materials, the course of the process(e) according to the invention can be illustrated by the equation below.

The formula (II) provides a general definition of the acyl halidesrequired as starting materials for carrying out the process (a)according to the invention. In this formula, A and X each preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred for these radicals. Hal preferablyrepresents fluorine, chlorine or bromine.

The acyl halides of the formula (II) are known or can be prepared byknown methods (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A0 589 313).

The formula (III) provides a general definition of the anilinederivatives required as reaction components for carrying out the process(a) according to the invention. In this formula Q, R, Z and m eachpreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred for these radicals or thisindex.

The aniline derivatives of the formula (III) are known or can beprepared by known methods (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589301, EP-A 0 371 950 and EP-A 0 292 990).

Suitable acid binders for carrying out the process (a) according to theinvention are all inorganic and organic bases which are customary forsuch reactions. Preference is given to using alkaline earth metal oralkali metal hydroxides, such as sodium hydroxide, calcium hydroxide,potassium hydroxide, or else ammonium hydroxide, alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate, alkali metal or alkaline earth metalacetates, such as sodium acetate, potassium acetate, calcium acetate,and also tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU). However, it isalso possible to carry out the reaction without additional acid binder,or to use the amine component in an excess, so that it simultaneouslyacts as acid binder.

Suitable diluents for carrying out the process (a) according to theinvention are all customary inert organic solvents. Preference is givento using optionally halogenated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decaline; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichloroethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol;nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters such as methyl acetate or ethylacetate; sulphoxides, such as dimethylsulphoxide, or sulphones, such assulpholane.

When carrying out the process (a) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and120° C., preferably between 10° C. and 100° C.

Both the process (a) according to the invention and the processes (b) to(e) according to the invention are generally carried out underatmospheric pressure. However, it is in each case also possible to carryout the reaction under elevated or reduced pressure.

When carrying out the process (a) according to the invention, generally1 mol or else an excess of aniline derivative of the formula (III) and 1to 3 mol of acid binder are employed per mole of acyl halide of theformula (II). However, it is also possible to employ the reactioncomponents in other ratios. Work-up is carried out by customary methods.In general, the reaction mixture is admixed with water, and the organicphase is separated off and, after drying, concentrated under reducedpressure. The residue that remains may, if appropriate, be freed of anyimpurities that may still be present by customary methods, such aschromatography or recrystallization.

The formula (IV) provides a general definition of the carbanilidederivatives required as starting materials for carrying out the process(b) according to the invention. In this formula A, R, X and m preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred for these radicals or this index. X² alsopreferably represents oxygen or sulphur.

The carbanilide derivatives of the formula (IV) are known or can beprepared by known methods. Thus, compounds of the formula (IV) areobtained when acyl halides of the formula

in which

A, X and Hal are each as defined above

are reacted with amino-phenols or aminothiophenols of the formula

in which

R, X² and m are each as defined above,

if appropriate in the presence of an acid binder, such as, for example,potassium carbonate or a tertiary amine, and if appropriate in thepresence of an inert organic diluent, such as, for example, toluene, attemperatures between 20° C. and 150° C.

The amino-phenols or aminothiophenols of the formula (XI) required asreaction components for carrying out the above process are known or canbe prepared by known methods.

The formula (V) provides a general definition of the compounds requiredas reaction components for carrying out the process (b) according to theinvention. In this formula, R²⁸, Z and p each preferably have thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred for these radicals or this index. Epreferably represents chlorine, bromine, iodine, methylsulphonyloxy,tolylsulphonyloxy or a radical of the formula R²⁹—O—SO₂—O— orR²⁹—O—CO—O—, in which R²⁹ represents alkyl having 1 to 4 carbon atomsand preferably represents methyl or ethyl.

The compounds of the formula (V) are also known or can be prepared byknown methods.

Suitable acid binders for carrying out the process (b) according to theinvention are all inorganic or organic bases which are customary forsuch reactions. Preference is given to using alkaline earth metal oralkali metal hydrides, hydroxides, amides, alkoxides, acetates,carbonates or bicarbonates, such as, for example, sodium hydride, sodiumamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide,sodium hydroxide, potassium hydroxide, sodium acetate, potassiumacetate, calcium acetate, sodium carbonate, potassium carbonate,potassium bicarbonate or sodium bicarbonate, furthermore ammoniumcompounds, such as ammonium hydroxide, ammonium acetate or ammoniumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out the process (b) according to theinvention are all customary inert organic solvents. Preference is givento using all those diluents which have already been mentioned inconnection with the description of the process (a) according to theinvention as being preferred.

When carrying out the process (b) according to the invention, thereaction temperatures may also be varied within a relatively wide range.In general, the process is carried out at temperatures between −20° C.and +150° C., preferably between −10° C. and +120° C.

When carrying out the process (b) according to the invention, generally1 to 2 mol of a compound of the formula (V) and, if appropriate, anequivalent amount or else an excess of acid binder are employed per moleof carbanilide derivative of the formula (IV). Work-up is carried out bycustomary methods. In general, the reaction mixture is admixed withwater and the organic phase is separated off and, after drying,concentrated under reduced pressure. If a water-miscible solvent isemployed for carrying out the reaction, the desired product is generallyobtained as a solid on dilution of the reaction mixture with water. Inthis case, the isolation is generally carried out by simple filteringoff with suction. The product which is obtained in each case can, ifappropriate, be freed of any impurities that may still be present bycustomary methods, such as chromatography or recrystallization.

The formula (VI) provides a general definition of the carbanilidederivatives required as starting materials for carrying out the process(c) according to the invention. In this formula, A, R, R²⁷, X and m eachpreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred for these radicals or thisindex. E¹ preferably represents chlorine, bromine, iodine,methylsulphonyloxy, tolylsulphonyloxy or a radical of the formulaR²⁹—O—SO₂—O— or R²⁹—O—CO—O— in which R²⁹ represents alkyl having 1 to 4carbon atoms and preferably represents methyl or ethyl.

The carbanilide derivatives of the formula (VI) are known or can beprepared by known methods.

The formula (VII) provides a general definition of the compoundsrequired as reaction components for carrying out the process (c)according to the invention. In this formula, R²⁸, Z and p eachpreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred for these radicals or thisindex. X³ also preferably represents oxygen or sulphur.

The compounds of the formula (VIII) are also known or can be prepared byknown methods.

Suitable acid binders for carrying out the process (c) according to theinvention are all inorganic and organic bases which are customary forsuch reactions. Preference is given to using all those acid acceptorswhich have already been mentioned in connection with the description ofthe process (b) according to the invention as being preferred.

Suitable diluents for carrying out the process (c) according to theinvention are water and all customary inert, organic solvents.Preference is given using aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, carbon tetrachloride, ethers, such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethyleneglycol dimethyl ether or ethylene glycol diethyl ether; ketones, such asacetone, butanone or methyl isobutyl ketone; nitriles, such asacetonitrile, propionitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamides; esters such asmethyl acetate or ethyl acetate, sulphoxides, such as dimethylsulphoxide, alcohols, such as methanol, ethanol, n- or i-propinole,ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,diethylene glycol monomethyl ether, diethylene glycol monoethyl ether,mixtures thereof with water or pure water.

When carrying out the process (c) according to the invention, thereaction temperatures may also be varied within a relatively wide range.In general, the process is carried out at temperatures between −20° C.and +150° C., preferably between −10° C. and +120° C.

When carrying out the process (c) according to the invention, generally1 to 2 mol of a compound of the formula (VII) and, if appropriate, anequivalent amount or else an excess of acid binder are employed per moleof carbanilide derivative of the formula (VI). Work-up is carried out bycustomary methods.

The formula (VIII) provides a general definition of the carbanilidederivatives required as starting materials for carrying out the process(d) according to the invention. In this formula, A, R, R²⁷, X and m eachpreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred for these radicals or thisindex.

The carbanilide derivatives of the formula (VIII) are known or can beprepared by known methods.

Suitable acid binders for carrying out the process (d) according to theinvention are all inorganic and organic bases which are customary forsuch reactions. Preference is given to using all those acid acceptorswhich have already been mentioned as being preferred in connection withthe description of the process (b) according to the invention.

Suitable diluents for carrying out the process (d) according to theinvention are all customary inert organic solvents. Preference is givento all those diluents which have already been mentioned as beingpreferred in connection with the description of the process (a)according to the invention.

When carrying out the process (d) according to the invention, thereaction temperatures may also be varied within a relatively wide range.In general, the process is carried out at temperatures between −20° C.and +150° C., preferably between −10° C. and +120° C.

When carrying out the process (d) according to the invention, generally1 to 2 mol of a compound of the formula (V) and, if appropriate, anequivalent amount or else an excess of acid binder are employed per moleof carbanilide derivative of the formula (VIII). Work-up is carried outby customary methods.

The formula (IX) provides a general definition of the carbanilidederivatives required as starting materials for carrying out the process(e) according to the invention. In this formula, A, R, R²⁶, X and m eachpreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred for these radicals or thisindex.

The carbanilide derivatives of the formula (IX) are known or can beprepared by known methods.

The formula (X) provides a general definition of the hydroxylaminederivatives required as reaction components for carrying out the processaccording to the invention. In this formula, Z preferably has thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred for this radical.

The hydroxylamine derivatives of the formula (X) are known or can beprepared by known methods.

Suitable catalysts for carrying out the process (e) according to theinvention are all acidic reaction promoters which are customary for suchreactions. Preference is given to using hydrogen chloride, sulphuricacid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid,methane sulphonic acid, trifluoromethanesulphonic acid, toluenesulphonicacid, boron trifluoride (also as etherate), boron tribromide, aluminumtrichloride, titanium tetrachloride, tetrabutylorthotitanate, zincchloride, iron(III) chloride, antimony pentachloride, acidic ionexchangers, acidic alumina and acidic silica gel.

Suitable diluents for carrying out process (e) according to theinvention are all inert organic solvents which are customary for suchreactions. Preference is given to using aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; furthermorehalogenated hydrocarbons such as chlorobenzene, dichlorobenzene,dichloromethane, chloroform, carbon tetrachloride, dichloroethane ortrichloroethane and also nitriles, such as n- or i-butyronitrile orbenzonitrile.

When carrying out the process (e) according to the invention, thereaction temperatures can also be varied within a relative wide range.In general, the process is carried out at temperatures between 0° C. and150° C., preferably between 20° C. and 120° C.

When carrying out the process (e) according to the invention, generally1 to 2 mol of hydroxylamine derivative of the formula (X) are employedper mole of carbanilide derivative of the formula (IX). Work-up iscarried out by customary methods.

The compounds according to the invention have a potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae,

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorumTilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling diseases in viticulture andfruit and vegetable growing, such as, for example, against Venturia,Podosphaera, Phytophthora and Plasmopara species. They are also verysuccessfully used for controlling rice diseases, such as, for example,Pyricularia species.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

The active compounds according to the invention are also suitable forcontrolling animal pests, in particular insects, arachnids andnematodes, which are encountered in agriculture, in forests, inhorticulture in the protection of stored products and of materials, andin the hygiene or veterinary medicine sector, and have good planttolerance and favorable toxicity to warm-blooded animals. The compoundsare active against normally sensitive and resistant species and againstpests in all or some stages of development. The abovementioned animalpests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Spodoptera litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp. and Trichodorus spp.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or elseprotein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations also mixed with known fungicides, bactericides,acaricides, nematicides or insecticides in order thus, for example, towiden the spectrum of action or to prevent development of resistance. Inmany cases, synergistic effects are achieved, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticdin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulphamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene(PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2-aminobutane,

2-phenylphenol (OPP)

8-hydroxyquinoline sulphate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,methanetetrathiol sodium salt

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methaneimideamide,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

2-chloro-N-(2,6-dimethylphenyl)-N-isothiocyanatomethyl)-acetamide,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

methyl N-(chloroacetyl )-N-(2,6-dimethylphenyl )-DL-alaninate,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

methyl N-(2,6-dimethylphenyl )-N-(5-isoxazolylcarbonyl)-DL-alaninate,

potassium hydrogen carbonate,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl)-1H-imidazole,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methaneamine,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaticides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,betacyluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth-promoting substances.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bypouring, spraying, atomizing, spreading, foaming, brushing on and thelike. It is further possible to apply the active compounds by theultra-low volume method or to inject the active compound formulation, orthe active compound itself, into the soil. The seed of the plants canalso be treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to 50g, preferably 0.01 to 10 g, are generally required per kilogram of seed.

In the treatment of the soil, active compound concentrations of from0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight,are required at the site of action.

The compositions used for the protection of industrial materialsgenerally comprise an amount of 1 to 95%, preferably 10 to 75%, of theactive compounds.

The use concentrations of the active compounds according to theinvention depend on the species and the occurrence of the microorganismsto be controlled and on the composition of the material to be protected.The optimal rate of application can be determined by test series. Ingeneral, the use concentrations are in the range from 0.001 to 5% byweight, preferably 0.05 to 1.0% by weight, based on the material to beprotected.

The activity and the activity spectrum of the active compounds which areto be used according to the invention in the protection of materials, orof the compositions, concentrates or quite generally formulations whichcan be prepared therefrom, can be increased by adding, if appropriate,further compounds having antimicrobial activity, fungicides,bactericides, herbicides, insecticides or other active compounds forwidening the activity spectrum or for achieving particular effects, suchas, for example, the additional protection against insects. Thesemixtures may have a wider spectrum of activity than the compoundsaccording to the invention.

Likewise, when used against animal pests the compounds according to theinvention may be present in commercial formulations, and in the useforms prepared from these formulations as a mixture with synergists.Synergists are compounds which increase the activity of the activecompounds, without it being necessary for the added synergist to beactive itself.

The content of active compound of the use forms prepared from thecommercial formulations can be varied within wide ranges. The activecompound concentration in the use forms can be from 0.0000001 to 95% byweight of active compound, preferably between 0.0001 and 1% by weight.

Application is carried out in a customary manner adapted to the useforms.

The preparation and the use of the compounds according to the inventionis illustrated by the examples below.

PREPARATION EXAMPLES Example 1

Process (a):

At room temperature, a solution of 0.3 g (0.0015 mol) of2-(2-phenyl-ethen-1-yl)-aniline in 2 ml of toluene is admixed with asolution of 0.15 g (0.0015 mol) of triethylamine in 10 ml of toluene. Atroom temperature, 0.33 g (0.0015 mol) of3-difluoromethoxy-thiophene-2-carbonyl chloride are added to thismixture with stirring. The mixture is subsequently heated to 50° C. andstirred at this temperature for 2 hours. For work-up, the reactionmixture is then cooled to room temperature and admixed with water. Theorganic phase is separated off, dried over sodium sulphate and thenconcentrated under reduced pressure at 60° C. The residue that remainsis chromatographed over silica gel using diethyl ether. Concentration ofthe eluate gives 0.53 g (95% of theory) of2-(2-phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilide inthe form of a solid substance of melting point 80 to 82° C.

At 80° C., a mixture of 4.2 g (0.022 mol) of3-difluoromethoxy-thiophene-2-carboxylic acid in 45 ml of toluene isadmixed with 3.1 g (0.026 mol) of thionyl chloride. After the additionhas ended, the reaction mixture is heated to 90° C. and stirred at thistemperature for another 2 hours. The reaction mixture is subsequentlyconcentrated under reduced pressure at 60° C. This gives 4.6 (98.3% oftheory) of 3-difluoromethoxy-thiophene-2-carbonyl chloride in the formof an oil.

At room temperature, a mixture of 2.4 g of (0.012 mol) of methyl3-difluoromethoxy-thiophene-2-carboxylate and 5 ml of ethanol is admixedwith a solution of 2 g (0.048 mol) of sodium hydroxide in 10 ml of waterand then stirred at room temperature for 10 hours. The reaction mixtureis then diluted with 50 ml of water and extracted repeatedly withmethylene chloride. The aqueous phase is adjusted to a pH of 2 to 3 byaddition of dilute hydrochloric acid. The resulting solid product isfiltered off with suction, washed with water and dried. This gives 2.2 g(90.15% of theory) of 3-difluoromethoxy-thiophene-2-carboxylic acid inthe form of a solid substance of melting point 98 to 100° C.

At room temperature, a mixture of 10 g (0.063 mol) of methyl3-hydroxy-thiophene-2-carboxylate and 90 ml of toluene is admixed with asolution of 5.1 g (0.127 mol) of sodium hydroxide in 8 ml of water. Thereaction mixture is heated with stirring to 90° C., 1.1 g oftetrabutyl-phosphonium bromide are added and 16.4 g (0.189 mol) ofchlorodifluoromethane are introduced over a period of 30 minutes. Themixture is then stirred at 90° C. for one hour. The reaction mixture issubsequently cooled to room temperature and admixed with water. Theorganic phase is separated off, dried over sodium sulphate and thenconcentrated under reduced pressure at 50° C. The residue that remainsis chromatographed over silica gel using cyclohexane:ethyl acetate=3:1as mobile phase. Concentration of the eluate gives 4.1 g (31.3% oftheory) of methyl 3-difluoromethoxy-thiophene-2-carboxylate in the formof an oil.

¹H NMR spectrum (CDCl₃/TMS): δ=3.833 (s, 3H); 7.463/7.481 (d, 1H) ppm

At room temperature, a mixture of 12.9 g (0.057 mol) of1-phenyl-2-(2-nitro-phenyl)-ethene and 210 ml of 17% strength aqueoushydrochloric acid is admixed with 38.7 g of tin powder and slowly heatedto reflux temperature. The mixture is boiled under reflux for 2 hoursand then cooled to room temperature and extracted repeatedly withdiethyl ether. The organic phase is concentrated under reduced pressure.The residue that remains is admixed with water, and the resultingmixture is neutralized by addition of dilute aqueous sodium hydroxidesolution and then extracted repeatedly with methylene chloride. Thecombined organic phases are dried over sodium sulphate and subsequentlyconcentrated under reduced pressure. The residue that remains ischromatographed over silica gel using cyclohexane: ethyl acetate=3:1.Concentration of the eluate gives 8.5 g (76.4% of theory) of2-(2-phenylethen-1-yl)-aniline in the form of a solid substance ofmelting point 80° C.

Example 2

Process (b):

At room temperature, a mixture of 1.0 g (0.0035 mol) of2-hydroxyphenyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide,0.53 g (0.0039 mol) of potassium carbonate and 10 ml of acetonitrile isadmixed with stirring with 0.57 g (0.0037 mol) of 2,4-dimethyl-benzylchloride. After the addition, the reaction mixture is heated to 60° C.and stirred at this temperature for 2 hours. The reaction mixture issubsequently cooled to room temperature and admixed with water. Theresulting precipitate is filtered off with suction, washed with waterand dried over phosphorus pentoxide at 50° C. under reduced pressure.This gives 1.2 g (85% of the theory) of2-(2,4-dimethyl-benzyloxy)-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilideas a solid substance of melting point 123 to 125° C.

¹H NMR spectrum (CDCl₃/TMS): δ=3.945 (s, 3H); 5.082 (s, 2H) ppm.

At 100° C., a mixture of 2.4 g (0.022 mol) of 2-amino-phenol and 80 mlof toluene is admixed with stirring with a solution of 5.0 g (0.0024mol) of 1-methyl-3-trifluoromethyl-pyrazole-4-carbonyl chloride in 25 mlof toluene. The reaction mixture is stirred at 100° C. for a further 4hours and then cooled to room temperature and admixed with water. Theresulting precipitate is filtered off with suction and dried underreduced pressure at 50° C. This gives 5.4 g (86.1% of theory) of2-hydroxyphenyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide inthe form of a solid substance of melting point 191° C.

¹H NMR spectrum (d6-DMSO/TMS): δ=3.972 (s, 3H)

Example 3

Process (b):

At 15° C., a solution of 3 g (10.5 mmol) of2-hydroxyphenyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide in15 ml of dimethylformamide is admixed slowly and with stirring with0.347 mg of sodium hydride (80% strength in paraffin). This mixture issubsequently added dropwise at 0° C. with stirring to a solution of 1.41g (10.5 mmol) of 4,5,6-trifluoropyrimidine in 15 ml ofdimethylformamide. After the addition has ended, the reaction mixture isstirred for another hour at 0° C. and then concentrated by removal ofthe solvent under reduced pressure. The residue that remains is admixedwith water and stirred vigorously for 2 minutes. The resulting solidproduct is filtered off with suction, dried and recrystallized fromtoluene. This gives 3.43 g (81% of theory) of2-(4,5-difluoro-pyrimidyl-6-oxy)-1-methyl-3-trifluoromethyl-1-pyrazole-4-carboxanilidein the form of a solid substance of melting point 197° C.

The carbanilides of the formula

listed in Table 1 below are also prepared by the methods mentionedabove.

TABLE 1 Ex. physic. No. A X Q Z R_(m) constant 4

O —CH═CH—

— m.p. 154-156° C. 5

O —CH═CH—

— m.p. 144-146° C. 6

O —SO₂—

— m.p. 97° C. 7

O —SO₂—

— ¹H NMR** δ = 2.55 (3H) 8

O O

— m.p. 68° C. 9

O O

— ¹H NMR** δ = 2.44 (3H) 3.82 (3H) 10

O O

— ¹H NMR** δ = 2.73 (3H) 11

O SO₂

— m.p. 94° C. 12

O O

— m.p. 95° C. 13

O SO₂

— m.p. 119° C. 14

O O

— Oil 15

O —CH═CH—

— Oil 16

O —CH═CH—

— m.p. 117° C. 17

O —CH═CH—

— m.p. 208° C. 18

O —CH═CH—

— m.p. 123° C. 19

O —CH═CH—

— m.p. 161° C. 20

O —CH═CH—

— m.p. 122° C. 21

O O

— m.p. 110-112° C. 22

O —CH═CH—

— m.p. 158° C. 23

O —CH═CH—

— ¹H NMR** δ = 2.30 (3H) 24

O —CH═CH—

— ¹H NMR** δ = 2.04 (3H) 25

O —CH═CH—

— ¹H NMR** δ = 2.40 (3H) 26

O —*O—CH₂—

— m.p. 113-115° C. 27

O —*O—CH₂—

— m.p. 108° C. 28

O —*O—CH₂—

— m.p. 123-125° C. 29

O —CH═CH—

— m.p. 177° C. 30

O —*O—CH₂—

— m.p. 123-126° C. 31

O —*O—CH₂—

— m.p. 90-92° C. 32

O —*O—CH₂—

— m.p. 83-85° C. 33

O —*O—CH₂—

— m.p. 105-107° C. 34

O —*O—CH₂—

— m.p. 89-91° C. 35

O —*O—CH₂—

— m.p. 158-161° C. 36

O —*CH₂—S—

— ¹H NMR** δ = 3.88 (3H); 4.12 (2H) 37

O —*CH₂—S—

— m.p. 105° C. 38

O —*CH₂—S—

— m.p. 78° C. 39

O —*CH₂—S—

— m.p. 131° C. 40

O —*CH₂—S—

— m.p. 97° C. 41

O —*CH₂—S—

— m.p. 99° C. 42

O —*CH₂—S—

— m.p. 94° C. 43

O —*CH₂—S—

— m.p. 135° C. 44

O —*CH₂—S—

— m.p. 118° C. 45

O —*CH₂—S—

— m.p. 161° C. 46

O —*CH₂—S—

— m.p. 108° C. 47

O —*O—CH₂—

— m.p. 73-75° C. 48

O —*O—CH₂—

— m.p. 98-100° C. 49

O —*O—CH₂—

— m.p. 88-90° C. 50

O —*CH₂—O—

— m.p. 120° C. 51

O —*CH₂—O—

— m.p. 112° C. 52

O —*CH₂—O—

— m.p. 153° C. 53

O —*CH₂—O—

— m.p. 167° C. 54

O —*CH₂—S—

— m.p. 108° C. 55

O —*CH₂—S—

— m.p. 131° C. 56

O —*O—CH₂—

— m.p. 104-106° C. 57

O —*O—CH₂—

— m.p. 130-133° C. 58

O —*CH₂—S—

— m.p. 133° C. 59

O —*CH₂—S—

— m.p. 133° C. 60

O —*CH₂—O—

— m.p. 153° C. 61

O —*CH₂—S—

— m.p. 112° C. 62

O —*O—CH₂—

— m.p. 129-131° C. 63

O —*O—CH₂—

— m.p. 137-138° C. 64

O —*O—CH₂—

— m.p. 128-130° C. 65

O —*CH₂—S—

— ¹H NMR** δ = 2.29 (3H); 4.09 (2H) 66

O —*O—CH₂—

— m.p. 118-120° C. 67

O —*O—CH₂—

— m.p. 158-159° C. 68

O —*O—CH₂—

— m.p. 98-100° C. 69

O —*O—CH₂—

— m.p. 112-114° C. 70

O —*CH₂—O—

— m.p. 149° C. 71

O —*O—CH₂—

— ¹H NMR** δ = 2.15 (3H) 72

O —*O—CH₂—

— m.p. 118° C. 73

O —*O—CH₂—

— m.p. 122° C. 74

O —*O—CH₂—

— ¹H NMR** δ = 2.25 (3H) 75

O —*O—CH₂—

— m.p. 110° C. 76

O —*O—CH₂—

— m.p. 76° C. 77

O —*O—CH₂—

— m.p. 135° C. 78

O —*O—CH₂—

— m.p. 94° C. 79

O —*CH₂—S—

— ¹H NMR** δ = 3.89 (3H) 4.08 (2H) 80

O —*CH₂—S—

— m.p. 169° C. 81

O —*CH₂—S—

— m.p. 119° C. 82

O —*CH₂—S—

— m.p. 155° C. 83

O —*CH₂—S—

— m.p. 115° C. 84

O —*CH₂—S—

— m.p. 97° C. 85

O —*CH₂—S—

— m.p. 112° C. 86

O —*O—CH₂—

— m.p. 140° C. 87

O —*O—CH₂—

— m.p. 115-118° C. 88

O —*O—CH₂—

— m.p. 165-168° C. 89

O —*O—CH₂—

— m.p. 182-184° C. 90

O —*CH₂—S—

— m.p. 116° C. 91

O —*CH₂—SO—

— m.p. 182° C. 92

O —*CH₂—SO—

— m.p. 165° C. 93

O —*CH₂—SO—

— m.p. 147° C. 94

O —*O—CH₂—

— m.p. 137° C. 95

O —*O—CH₂—

— m.p. 76-78° C. 96

O —*O—CH₂—

— m.p. 130-132° C. 97

O —*O—CH₂—

— m.p. 113-115° C. 98

O —*O—CH₂—

— m.p. 118° C. 99

O —*O—CH₂—

— m.p. 95° C. 100

O —*O—CH₂—

— m.p. 81-82° C. 101

O —*O—CH₂—

— m.p. 95° C. 102

O —*O—CH₂—

— m.p. 124° C. 103

O —*O—CH₂—

— m.p. 149-150° C. 104

O —*O—CH₂—

— m.p. 60-62° C. 105

O —*CH₂—SO₂—

— m.p. 211° C. 106

O —*CH₂—SO₂—

— m.p. 162° C. 107

O —*CH₂—SO₂—

— ¹H NMR** δ = 3.93 (3H); 4.36 (2H) 108

O —*CH₂—SO₂—

— m.p. 165° C. 109

O —*O—CH₂—

— m.p. 166-168° C. 110

O —*O—CH₂—

— m.p. 157-158° C. 111

O —*O—CH₂—

— m.p. 92° C. 112

O —*O—CH₂—

— m.p. 108° C. 113

O —*O—CH₂—

— m.p. 118-120° C. 114

O O

— ¹H NMR** δ = 9.61 (1H, s) 115

O —*CH₂—O—

— ¹H NMR** δ = 5.10 (2H, s) 116

O —*CH₂—O—

— ¹H NMR** δ = 5.07 (1H, s) 117

O —*CH₂—O—

— ¹H NMR** δ = 2.29 (3H, s) 118

O —*CH₂—O—

— ¹H NMR** δ = 2.30 (3H) 119

O —*CH₂—O—

— ¹H NMR** δ = 3.83 (3H) 120

O —*CH₂—O—

— ¹H NMR** δ = 3.66 (3H) 121

O —*CH₂—O—

— ¹H NMR** δ = 5.10 (2H) 122

O —*CH₂—O—

— ¹H NMR** δ = 2.73 (3H) 123

O —*CH₂—O—

— ¹H NMR** δ = 3.81 (3H) 124

O —*CH₂—O—

— ¹H NMR** δ = 5.08 (2H) 125

O *—CH₂—O—

— ¹H NMR** δ = 2.73 (3H) 126

O —*CH₂—O—

— ¹H NMR** δ = 5.12 (2H) 127

O —*CH₂—O—

— ¹H NMR** δ = 2.26 (3H) 128

O —*CH₂—O—

— ¹H NMR** δ = 1.86 (3H) 129

O —*CH₂—O—

— ¹H NMR** δ = 2.24 (3H) 130

O —*CH₂—O—

— ¹H NMR** δ = 5.13 (2H) 131

O —*CH₂—O—

— ¹H NMR** δ = 3.69 (3H) 132

O —*CH₂—O—

— ¹H NMR** δ = 3.87 (3H) 133

O —*CH₂—O—

— ¹H NMR** δ = 3.87 (3H) 134

O —*CH₂—O—

— ¹H NMR** δ = 2.73 (3H) 135

O —*CH₂—O—

— ¹H NMR** δ = 5.14 (2H) 136

O —*CH₂—O—

— ¹H NMR** δ = 2.06 (3H) 137

O —*CH₂—O—

— ¹H NMR** δ = 5.11 (2H) 138

O —*CH₂—O—

— ¹H NMR** δ = 3.73 (3H) 139

O —*CH₂—O—

— ¹H NMR** δ = 3.81 (3H) 140

O —*CH₂—O—

— ¹H NMR** δ = 5.09 (2H) 141

O —*CH₂—O—

— ¹H NMR** δ = 2.26 (3H) 142

O —*CH₂—O—

— ¹H NMR** δ = 5.26 (2H) 143

O —*CH₂—O—

— ¹H NMR** δ = 2.29 (3H) 144

O —*CH₂—O—

— ¹H NMR** δ = 5.05 (3H) 145

O —*CH₂—O—

— ¹H NMR** δ = 3.75 (3H) 146

O —*CH₂—O—

— ¹H NMR** δ = 5.04 (2H) 147

O —*CH₂—O—

— ¹H NMR** δ = 5.07 (3H) 148

O —*CH₂—O—

— m.p. 122° C. 149

O —*CH₂—SO—

— m.p. 69° C. 150

O O

— ¹H NMR** δ = 2.39 (3H) 151

O

— m.p. 166° C. 152

O O

— m.p. 112-114° C. 153

O

— m.p. 165° C. 154

O O

— m.p. 109-111° C. 155

O

— m.p. 95-98° C. 156

O

— m.p. 133-135° C. 157

O

— m.p. 160° C. 158

O

— m.p. 178° C. 159

O

— m.p. 112° C. 160

O

— m.p. 133° C. 161

O

— m.p. 147° C. 162

O

— m.p. 63° C. 163

O

— m.p. 142° C. 164

O

— m.p. 145-148° C. 165

O —CH═CH—

— m.p. 133° C. 166

O —CH═CH—

— m.p. 70-72° C. 167

O

— n_(D) ²⁰ = 1.5921 168

O O

— m.p. 100° C. 169

O

— n_(D) ²⁰ = 1.5985 170

O —*CH₂—O—

— m.p. 112° C. 171

O —*CH₂—O—

— m.p. 94° C. 172

O —*CH₂—O—

— m.p. 109° C. 173

O —*CH₂—O—

— m.p. 79° C. 174

O —*CH₂—O—

— m.p. 99° C. 175

O —*CH₂—O—

— m.p. 110° C. 176

O —*CH₂—O—

— ¹H NMR** δ = 5.02 (2H) 177

O —*CH₂—O—

— ¹H NMR** δ = 5.06 (2H) 178

O —*CH₂—O—

— m.p. 120° C. 179

O —*CH₂—O—

— ¹H NMR** δ = 5.06 (2H) 180

O —*CH₂—O—

— ¹H NMR** δ = 5.09 (2H) 181

O —*CH₂—O—

— m.p. 115° C. 182

O —*CH₂—O—

— ¹H NMR** δ = 5.18 (2H) 183

O —*CH₂—O—

— m.p. 114° C. 184

O —*CH₂—O—

— m.p. 104° C. 185

O —*CH₂—O—

— m.p. 137° C. 186

O —*CH₂—O—

— m.p. 124° C. 187

O —*CH₂—O—

— m.p. 103° C. 188

O —*CH₂—O—

— ¹H NMR** δ = 5.06 (2H) 189

O —*CH₂—O—

— ¹H NMR** δ = 5.05 (2H) 190

O —*CH₂—O—

— m.p. 143° C. 191

O —*CH₂—O—

— ¹H NMR** δ = 2.75 (3H) 192

O —*CH₂—O—

— m.p. 99° C. 193

O —*CH₂—O—

— ¹H NMR** δ = 2.27 (3H) 194

O —*CH₂—O—

— m.p. 116° C. 195

O —*CH₂—O—

— m.p. 88-90° C. 196

O O

— m/e = 479 197

O O

— m/e = 397 λ_(max) = 262 mμ 198

O —*CH₂—O—

— m.p. 131° C. 199

O

— m.p. 94° C. 200

O

— m.p. 120° C. 201

O

— m.p. 136° C. 202

O

— m.p. 105° C. 203

O

— m.p. 76° C. 204

O

— m.p. 97° C. 205

O —*CH₂—O—

— m/e = 369 λ_(max) = 293 mμ 206

O O

— ¹H NMR** δ = 2.60 (3H) 207

O O

— m.p. 104° C. 208

O —CH═CH—

— m.p. 123° C. 209

O —*CH₂—O—

— ¹H NMR** δ = 5.12 (2H) 210

O

— m.p. 143° C. 211

O —*CH₂—O—

— ¹H NMR** δ = 2.30 (3H) 212

O —*CH₂—O—

— m.p. 111° C. 213

O O

— m.p. 99° C. 214

O O

— m.p. 75° C. 215

O O

— m.p. 95° C. *)The molecular moiety labelled (*) is in each caseattached to the phenyl radical of the aniline moiety. **)The ¹H NMRspectra were recorded in deuterochloroform (CDCl₃) using tetramethylsilane (TMS) as internal standard. The chemical shift as δ value in ppmis given.

USE EXAMPLES Example A

Podosphaera test (apple)/protective Solvent: 47 parts by weight ofacetone Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray-coatinghas dried on, the plants are inoculated by dusting with conidia of thecausative organism of apple mildew Podosphaera leucotricha.

The plants are then placed in a greenhouse at 23° C. and a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE A Podosphaera test (apple)/protective Efficacy in % at an activecompound concentration in Active compound the spray liquor of 100 ppmAccording to the invention:

100

96

Example B

Venturia test (apple)/protective Solvent: 47 parts by weight of acetoneEmulsifier: 3 parts by weight of alkyaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray-coatinghas dried on, the plants are inoculated with an aqueous conidiasuspension of the causative organism of apple scab Venturia inaequalisand then remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 23° C. and a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE B Venturia test (apple)/protective Efficacy in % at an activecompound concentration in Active compound the spray liquor of 100 ppmAccording to the invention:

83

83

94

97

100

100

95

90

Example C

Pyrenophora teres test (barley)/protective Solvent: 10 parts by weightof N-methyl-pyrrolidone Emulsifier: 0.6 parts by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray-coating has dried on, the plants are sprayed with aconidia suspension of Pyrenophora teres.

The plants remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of approximately20° C. in a relative atmospheric humidity of approximately 80%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE C Pyrenophora teres test (barley)/protective Application rate ofactive compound in Active compound g/ha Efficacy in % According to theinvention:

125 83

125 75

Example D

Pseudocercosporella herpotrichoides test; R-strain (wheat)/protectiveSolvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier: 0.6parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at stated application rates.

After the spray-coating has dried on, the plants are inoculated at thebase of the stem with spores of the R-strain of Pseudocercosporellaherotrichoides.

The plants are placed in a greenhouse at a temperature of approximately10° C. and a relative atmospheric humidity of approximately 80%.

Evaluation is carried out 21 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE D Pseudocercosperella herpotrichoides test; R-strain(wheat)/protective Application rate of active compound in EfficacyActive compound g/ha in % According to the invention:

250 90

Example E

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of diamond-back moth (Plutella maculipennis)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all the caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE E Plutella test Active compound concentration in Degree of killActive compound % in % after 7 d According to the invention:

0.1 100

0.1 100

0.1 100

0.1 100

0.1 100

0.1 90

0.1 100

Example F

Spodopteta test Solvent: 7 parts by weight of dimethylformamideEmulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the owlett moth (Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all the caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE F Spodoptera test Active compound concentration in Degree of killActive compound % in % after 7 d According to the invention:

0.1 100

Example G

Myzus test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by peachaphids (Myzus persicae) are treated by being dipped into the preparationof active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all the aphids have been killed, 0% means that none of theaphids have been killed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE G Myzus Test Active compound concentration Degree of kill Activecompound in % in % after 7 d According to the invention:

0.1 95

Example H

Inhibitory test with giant colonies of Basidiomycetes.

Solvent: Dimethyl sulphoxide

To produce a suitable preparation of active compound, 0.2 parts byweight of active compound are admixed with 99.8 parts by weight of theabovementioned solvent.

An agar which has been prepared using malt extract peptone is mixed inthe liquid state with the preparation of active compound at theparticular desired application rate. After the agar has set, theresulting nutrient medium is incubated at 26° C. with pieces of myceliumwhich had been punched out of colonies of Coniophora puteana or Coriolusversicolor.

Evaluation is carried out after 3 or 7 days' storage at 26° C. bymeasuring the growth of the hypha and scoring the resulting inhibitionin per cent in comparison to the untreated control. 0% means aninhibition of growth which corresponds to that of the untreated control,while an inhibition of growth of 100% means that no growth of the hyphais observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE H Inhibitory test with giant colonies of Basidiomycetes Inhibitionof the growth of the hypha in % with Coniophora puteana at an Coriolusversicolor at an Active active compound active compound compound ofconcentration of concentration of Example No. 1 ppm 3 ppm 6 ppm 1 ppm 3ppm 6 ppm 5 70 80 100 70 90 100 16 80 100 100 100 100 100 18 70 100 10070 100 100 20 100 100 100 100 100 100 39 70 80 90 90 100 100 40 50 60 7040 70 90 45 70 80 90 90 100 100 46 80 100 100 100 100 100 50 100 100 100100 100 100 52 80 90 100 90 100 100 78 70 80 90 90 90 100 81 70 90 10090 90 100 84 80 80 100 90 100 100 85 70 80 80 70 70 90 119 100 100 100100 100 100 123 100 100 100 100 100 100 139 100 100 100 100 100 100 14180 100 100 90 100 100 142 70 90 100 90 90 100 143 80 90 100 100 100 100144 70 90 100 90 100 100

Example J

Plasmopara test (grape vines)/protective Solvent: 47 parts by weight ofacetone Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray-coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at approximately 20° C. and 100% relative atmospheric humidity for1 day. The plants are subsequently placed in a greenhouse atapproximately 21° C. and approximately 90% relative atmospheric humidityfor 5 days. The plants are then moistened and placed in an incubationcabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE J Plasmopara test (grape vines)/protective Application rate ofactive compound in Active compound g/ha Efficacy in % According to theinvention:

100 95

100 90

Example K

Venturia test (apple)/protective Solution: 47 parts by weight of acetoneEmulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray-coating has dried on, the plants are inoculated with an aqueousConidia suspension of the causative organism of apple scab Venturiainaequalis and then remain in an incubation cabin at approximately 20°C. and 100% relative atmospheric humidity for 1 day.

The plants are subsequently placed in a greenhouse at approximately 21°C. and a relative atmospheric humidity of approximately 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE K Venturia test (apple)/protective Application rate of activecompound in Efficacy Active compound g/ha in % According to theinvention:

100 100

What is claimed is:
 1. A carbanilide of the formula

wherein R represents fluorine, chlorine, bromine, nitro, cyano, alkylhaving 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbonatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, alkenyloxy having 2 to 6 atoms,alkinyloxy having 2 to 6 atoms, cycloalkyl having 3 to 7 carbon atoms,carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or representsalkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, m represents the numbers 0, 1, 2 or3, where R represents identical or different radicals if m represents 2or 3, A represents a radical of the formula

R¹ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,isopropyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5fluorine, chlorine and/or bromine atoms and R² represents hydrogen,fluorine, chlorine, bromine, iodine, methyl or ethyl, Q representsalkylene having 1 to 3 carbon atoms, alkenylene having 2 or 3 carbonatoms, alkinylene having 2 or 3 carbon atoms or represents a group ofthe formula

R²⁴ and R²⁵ independently of one another each represent hydrogen,methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, alkenyl having 2 or3 carbon atoms or alkinyl having 2 or 3 carbon atoms, or Q represents agroup of the formula

R²⁷ and R²⁸ independently of one another each represent hydrogen, methylor ethyl, Y represents an oxygen atom or represents S(O)_(r) where rrepresents the numbers 0, 1 or 2 and n and p independently of oneanother each represent the numbers 0, 1 or 2, where the molecular moietylabeled (*) is in each case attached to the phenyl radical of theaniline moiety, X represents oxygen or sulphur, Z represents phenyl,naphthyl or anthracenyl, where each of these radicals may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, alkyl having 1 to 4 carbon atoms, alkylthiohaving 1 to 4 carbon atoms, halogenoalkyl having 1 to 5 fluorine,chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2 carbon atomsand 1 to 5 fluorine, chlorine and/or bromine atoms, phenyl and phenoxy,or Z represents hetaryl having 5 or 6 ring members and 1 to 3heteroatoms, selected from the group consisting of oxygen, sulphurand/or nitrogen, where each of the heterocycles may be mono- ordisubstituted by identical or different substituents selected from thegroup consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbonatoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbonatoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine,chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2 carbon atomsand 1 to 5 fluorine, chlorine and/or bromine atoms, phenyl and phenoxy.2. A pesticide composition comprising at least one carbanilide of claim1 and one or more extenders and/or surfactants.
 3. A method forcontrolling pests, comprising the step of applying an effective amountof the carbanilide of claim 1 to the pests and/or their habitat.
 4. Acarbanilide of the formula: